What Could Go Right?

There’s a question I’ve asked at the end of hundreds of podcast conversations.

“What advice would you give your younger self?”

It’s a simple question—but it tends to open something deeper. Almost everyone pauses. Almost everyone softens. And almost everyone, in one way or another, says something about perspective… about what they worried about… about how things turned out differently than they imagined.

Recently, I’ve found myself sitting with my own answer.

And I’ll be honest—I hesitate to use this word, but it feels right.

Convicted.

Not in a heavy or shame-filled way, but in a clear, illuminating kind of way. Like a light being turned on in a room I didn’t realize was dim.

I can see now that in many of my younger years, I didn’t live in the realm of possibility the way I wish I had.

I lived… cautiously.

Carefully.

Sometimes even fearfully.

And yet, when I look back, something almost frustratingly simple reveals itself:

Things tend to work out.

Not perfectly. Not without challenge. But rarely—almost never—as bad as I once imagined they might be.

Which brings me to a question I’ve been asking myself lately:

Who’s driving?

Who has their foot on the gas?

Who’s holding the wheel?

Is it fear… or is it possibility?

Because if I’m honest, fear has a way of quietly taking control. It doesn’t announce itself. It doesn’t say, “Hey, I’m about to limit your life.” It just starts asking a different set of questions:

What could go wrong?
What if this fails?
What will people think?

And if you follow those questions long enough, they’ll take you somewhere. Just not somewhere you really want to go.

But there’s another way.

A different posture.

A different question.

What could go right?

It almost feels too simple. Maybe even naïve at first glance. But I’m beginning to believe it might be one of the most powerful questions we can carry into our days.

Because when you ask what could go right, something shifts.

Your attention changes.

Your awareness opens.

You begin to notice opportunities instead of obstacles… people instead of problems… moments instead of missed chances.

You start to live in a way that welcomes things rather than forces them.

Love.

Connection.

Service.

Serendipity.

It’s less about controlling outcomes and more about being available to them.

Available for the right conversation.
Available for the unexpected introduction.
Available for the quiet nudge that says, “Go here… reach out… say yes.”

In many ways, it’s not about becoming someone new.

It’s about returning to something we’ve always known:

That life tends to meet us in the posture we bring to it.

So this weekend, maybe the invitation is simple.

Not to ignore reality.
Not to pretend challenges don’t exist.

But to gently, intentionally shift the question.

From what could go wrong…
to

what could go right?

You might be surprised where it leads.

Enjoy the Masters,

Ashton